10 Real-Life Wrestling Heels Who Turned Babyface

9. Bob Holly

Triple H Enemy Saviour
WWE.com

Was a heel because...

Beat the piss out of poor Matt Cappotelli on Tough Enough in an infamous, disturbing scene. He bust his lip and blackened his eye in the sort of mettle-testing practise that existed everywhere, once upon a time, but was shocking and ugly to witness on television. The screen literally brought this into focus, and Matt's sweetheart nature made him even more sympathetic. This was consistent with Holly's reputation as a liberty-taker which, contrasted with his ability and position on the card, compelled many to label him a cat-kicking prick who took it out on the green and the nervous.

Turned babyface by...

He was a prick, but he was top bantz. It might just be because Holly has such an abrupt, angry comedic quality about him, but the likes of Edge and Frankie Kazarian often pop themselves when recalling their dealings with the man. Perhaps Holly was WWE's Albert Rosenfield, a proponent of tough love on a mission more noble than you or I can conceive: the sanctity of professional wrestling.

Actually, Holly once called Michael Cole a "sh*thead" at WrestleMania.

Was he ever a heel?

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Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!